Ribosylnicotinamide Triflate

Base Information

• Chemical Name: Ribosylnicotinamide Triflate
• CAS No.: 445489-49-6
• Molecular Formula: C12H17F3N2O9S
• Molecular Weight: 422.3315896
• DSSTox Substance ID: DTXSID20462505
• Mol file: 445489-49-6.mol

Synonyms:445489-49-6;Nicotinamide Riboside Triflate;445489-49-6 (Triflate);Ribosylnicotinamide Triflate;3-(Aminocarbonyl)-1-B-D-ribofuranosyl-pyridinium Trifluoromethanesulfonic Acid;1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxamide;trifluoromethanesulfonate;Nicotinamide Ribose Triflate;SCHEMBL18444286;DTXSID20462505;ZEWRNTDQENDMQK-IVOJBTPCSA-N;AMY18811;AKOS027325536;Nicotinamide Riboside Triflate, alpha / beta mixture;3-Carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate;3-Carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-iumtrifluoromethanesulfonate;Pyridinium,3-?(aminocarbonyl)?-?1-?|A-?D-?ribofuranosyl-?,salt with trifluoromethanesulf?onic acid

Chemical Property of Ribosylnicotinamide Triflate

Chemical Property:

• PSA: 183.46000
• LogP: -0.08400
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 404.05012110
• Heavy Atom Count: 26
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

NicotinamideRibosideTriflate,α/βmixture ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C[N+](=C1)C2C(C(C(O2)CO)O)O)C(=O)N.C(F)(F)(F)S(=O)(=O)[O-]
• Isomeric SMILES: C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N.C(F)(F)(F)S(=O)(=O)[O-]
• Uses: Nicotinamide (N407750) analog. Nicotinamide riboside (β-NAR) is an intermediate in one biosynthetic pathway by which Nicotamide is converted into NAD (Nicotinamide Adenine Dinucleotide) Nicotinamide analog. Nicotinamide riboside (β-NAR) is an intermediate in one biosynthetic pathway by which Nicotamide is converted into NAD (Nicotinamide Adenine Dinucleotide)

Technology Process of Ribosylnicotinamide Triflate

There total 10 articles about Ribosylnicotinamide Triflate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

→ 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate (445489-49-6)

Guidance literature:

In water; at 20 ℃; for 1h;

Reference yield: 97.0%

3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate → 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate (445489-49-6)

Guidance literature:

With ammonium hydroxide; In methanol; water; at 0 ℃; for 6h; Inert atmosphere;

Reference yield:

nicotinamide (98-92-0,1255150-40-3) → 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate (445489-49-6)

Guidance literature:

Multi-step reaction with 3 steps

1: hexamethyldisilazane / 5 h / 120 °C

2: 93 percent / 1,2-dichloro-ethane / 2 h / 45 °C

3: NH₃ / methanol / 48 h / -5 °C

With ammonia; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2004.06.093

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

nicotinamide

N,N-bis(trimethylsilyl)nicotinamide

1,2,3,5-tetraacetylribose

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